RONICICLIB

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C18H21F3N4O3S
Molecular Weight	430.445
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@@H](O)[C@@H](C)OC1=NC(NC2=CC=C(C=C2)[S@](=N)(=O)C3CC3)=NC=C1C(F)(F)F

InChI

InChIKey=UELYDGOOJPRWGF-SRQXXRKNSA-N

InChI=1S/C18H21F3N4O3S/c1-10(26)11(2)28-16-15(18(19,20)21)9-23-17(25-16)24-12-3-5-13(6-4-12)29(22,27)14-7-8-14/h3-6,9-11,14,22,26H,7-8H2,1-2H3,(H,23,24,25)/t10-,11-,29+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C18H21F3N4O3S
Molecular Weight	430.445
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/30677506 | https://www.ncbi.nlm.nih.gov/pubmed/30089585 | https://clinicaltrials.gov/ct2/show/NCT02047890 | https://clinicaltrials.gov/ct2/show/NCT01573338 | https://clinicaltrials.gov/ct2/show/NCT02161419

Roniciclib (BAY1000394) is a pan-cyclin-dependent kinase inhibitor that has been developed for treatment in small cell lung carcinoma and solid tumors. Roniciclib targets certain key proteins that are essential for the survival of cancer cells, resulting in decreased tumor growth. Phase I studies to evaluate the safety, tolerability and pharmacokinetics of roniciclib have been completed successfully. In phase II studies, roniciclib was found to be well tolerated and showed promising efficacy when combined with chemotherapy in small cell lung carcinoma patients. However, due to an observed safety signal (treatment-emergent adverse events) in one phase II study, other clinical trials have been discontinued and further development of roniciclib was terminated.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Cyclin-dependent kinase 1/cyclin B 5 Target ID: CHEMBL2094127 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22821149	Inhibitor 8297	7.0 nM [IC50]
Cyclin-dependent kinase 2/cyclin E 10 Target ID: CHEMBL2094126 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22821149	Inhibitor 8297	9.0 nM [IC50]
Cyclin-dependent kinase 4/cyclin D 2 Target ID: CHEMBL2095942 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22821149	Inhibitor 8297	11.0 nM [IC50]
CDK9/cyclin T1 4 Target ID: CHEMBL2111389 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22821149	Inhibitor 8297	5.0 nM [IC50]

PubMed

Title	Date	PubMed
The lab oddity prevails: discovery of pan-CDK inhibitor (R)-S-cyclopropyl-S-(4-{[4-{[(1R,2R)-2-hydroxy-1-methylpropyl]oxy}-5-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)sulfoximide (BAY 1000394) for the treatment of cancer.	2013 Jul	23671017

Patents

Substance Class	Chemical Created by `admin` on `Sat Dec 16 05:09:29 UTC 2023` Edited by `admin` on `Sat Dec 16 05:09:29 UTC 2023`
Record UNII	0W9Q8U337A
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

RONICICLIB

Official Name

English

BAY1000394

Code

English

BAY10-00394

Code

English

BAY-1000394

Code

English

2-BUTANOL, 3-((2-((4-((S(R))-S-CYCLOPROPYLSULFONIMIDOYL)PHENYL)AMINO)-5-(TRIFLUOROMETHYL)-4-PYRIMIDINYL)OXY)-, (2R,3R)-

Common Name

English

roniciclib [INN]

Common Name

English

(R)-S-CYCLOPROPYL-S-(4-((4-(((1R,2R)-2-HYDROXY-1-METHYLPROPYL)OXY)-5-(TRIFLUOROMETHYL)PYRIMIDIN-2-YL)AMINO)PHENYL)SULFOXIMIDE

Systematic Name

English

Roniciclib [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C2185